Total synthesis of D-glycero-D-mannno-heptose 1β, 7-bisphosphate with 3-O-amyl amine linker and its monophosphate derivative
- Resource Type
- Authors
- Junjie Fu; Peter H. Seeberger; Jing Hu; Chunjun Qin; Jian Yin; Guangzong Tian; Oren Moscovitz; Xiaopeng Zou
- Source
- Chinese Journal of Natural Medicines. 18:628-632
- Subject
- Lipopolysaccharides
Anomer
Stereochemistry
Heptose
Alkylation
01 natural sciences
03 medical and health sciences
chemistry.chemical_compound
0302 clinical medicine
Gram-Negative Bacteria
Drug Discovery
Organotin Compounds
Amines
chemistry.chemical_classification
010405 organic chemistry
Chemistry
Total synthesis
General Medicine
Heptoses
0104 chemical sciences
Complementary and alternative medicine
030220 oncology & carcinogenesis
Phosphodiester bond
Amine gas treating
Linker
Derivative (chemistry)
- Language
- ISSN
- 1875-5364
D-Glycero-D-mannno-heptose 1β, 7-bisphosphate (HBPβ) is an important intermediate for constructing the core structure of Gram-negative bacterial lipopolysaccharides and was reported as a pathogen-associated molecular pattern (PAMP) that regulates immune responses. HBPβ with 3-O-amyl amine linker and its monophosphate derivative D-glycero-D-mannno-heptose 7-phosphate (HP) with 1α-amyl amine linker have been synthesized as candidates for immunity study of HBPβ. The O3-amyl amine linker of heptose was installed by dibutyltin oxide-mediated regioselective alkylation under fine-tuned protecting condition. The stereoselective installation of 1β-phosphate ester was achieved by NIS-mediated phosphorylation at low temperature. The strategy for installation of 3-O-amyl amine linker onto HBP derivative can be expanded to the syntheses of other conjugation-ready carbohydrates bearing anomeric phosphoester.